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Compound Detail

CHEMBL218693

CARNOSOL
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CC(C)c1cc2c(c(O)c1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL218693
Name CARNOSOL
Phase Preclinical
Structure Type MOL
InChI Key XUSYGBPHQBWGAD-PJSUUKDQSA-N
7
Targets
10
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

330.4
MW (Da)
4.29
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.60
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H26O4
MW 330.42
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 2.67

Activity Summary

IC50 10 meas. best 5.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin E synthase
CHEMBL5658
 IC50 5.3 5.3 5000.0 2
Pancreatic triacylglycerol lipase
CHEMBL1812
 IC50 4.89 4.89 13000.0 1
Farnesyl pyrophosphate synthase
CHEMBL1782
 IC50 4.88 4.88 13300.0 1
MCF7
CHEMBL387
 IC50 4.39 4.37 40900.0 2
HeLa
CHEMBL399
 IC50 4.36 4.36 43900.0 1
A549
CHEMBL392
 IC50 4.33 4.33 47000.0 1
Vero
CHEMBL391
 IC50 4.29 4.29 51500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin E synthase IC50 = 5000.0 nM 5.3 Inhibition of microsomal PGES1 in ILbeta-stimulated human A549 cells using PGH2 ... -
Prostaglandin E synthase IC50 = 5000.0 nM 5.3 Inhibition of mPGES1 in human A549 cell microsomal membrane using pGH2 as substr... 29329790
Pancreatic triacylglycerol lipase IC50 = 13000.0 nM 4.89 Inhibition of pancreatic lipase 17521912
Farnesyl pyrophosphate synthase IC50 = 13300.0 nM 4.88 Inhibition of human N-terminal TEV protease cleavage site-fused-His6-tagged FPPS... 31725297
MCF7 IC50 = 40900.0 nM 4.39 Cytotoxicity against human MCF7 cells at lag phase of growth after 48 hrs by MTT... 19711987
HeLa IC50 = 43900.0 nM 4.36 Cytotoxicity against human HeLa cells at lag phase of growth after 48 hrs by MTT... 19711987
MCF7 IC50 = 44500.0 nM 4.35 Cytotoxicity against human sMCF7 cells at exponential phase of growth after 48 h... 19711987
A549 IC50 = 47000.0 nM 4.33 Cytotoxicity against human A549 cells at exponential phase of growth after 48 hr... 19711987
Vero IC50 = 51500.0 nM 4.29 Cytotoxicity against african green monkey Vero cells at exponential phase of gro... 19711987

Literature References

PubMed DOI Target Context # Activities
23507152 10.1016/j.bmc.2013.02.019 Nuclear factor erythroid 2-related factor 2 6
33378620 10.1021/acs.jnatprod.0c00832 Pectobacterium carotovorum 4
33378620 10.1021/acs.jnatprod.0c00832 Listeria monocytogenes 4
33378620 10.1021/acs.jnatprod.0c00832 Staphylococcus aureus 4
33378620 10.1021/acs.jnatprod.0c00832 Acinetobacter baumannii 4
33378620 10.1021/acs.jnatprod.0c00832 Escherichia coli 4
33378620 10.1021/acs.jnatprod.0c00832 Pseudomonas aeruginosa 4
19711987 10.1021/np900047p HEp-2 2
19711987 10.1021/np900047p Vero 2
19711987 10.1021/np900047p A549 2
19711987 10.1021/np900047p MCF7 2
19711987 10.1021/np900047p HeLa 2
26241873 10.1016/j.ejmech.2015.07.034 MDA-MB-231 2
17190465 10.1021/np060279i T47D 1
19711987 10.1021/np900047p Pseudomonas aeruginosa 1
19711987 10.1021/np900047p Salmonella 1
17190465 10.1021/np060279i HBL-100 1
17190465 10.1021/np060279i A2780 1
8229021 10.1021/np50098a031 Unchecked 1
8229021 10.1021/np50098a031 Cathepsin D 1

Data from ChEMBL 36 via Core Engine